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Nucleotide analogs

  • US 5,656,745 A
  • Filed: 09/17/1993
  • Issued: 08/12/1997
  • Est. Priority Date: 09/17/1993
  • Status: Expired due to Term
First Claim
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1. A compound of the formula IIb ##STR23## wherein n is an integer having a value from 1 to 5 and if n>

  • 1, each --C(R3)(R2)-- may be the same or different;

    n1 is an integer;

    R1 is H or C1 -C9 alkyl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N, COOR4 and halogen, C3 -C6 aryl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N, COOR4 and halogen or C3 -C9 aryl-alkyl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N, COOR4 and halogen;

    R2 is independently H or C1 -C9 alkyl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N, COOR4 and halogen, C3 -C6 aryl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N, COOR4 and halogen or C3 -C9 aryl-alkyl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N, COOR4 and halogen;

    R3 is independently C(O)--OR4, amino, C1 -C3 alkylamino, C1 -C3 alkyldiamino, C1 -C6 alkenylamino, hydroxy, thiol, C1 -C3 alkoxy, C1 -C3 alkthiol, (CH2)n COOR4, alkoxyphenyl, C1 -C6 alkyl, C2 -C6 alkenyl, C6 -C12 aryl which is substituted or unsubstituted with OH, halogen, SH, NH2, phenyl, hydroxyphenyl or alkoxyphenyl;

    R4 is H provided that n1 is greater than 1, or is C3 -C9 alkyl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N and halogen, C3 -C6 aryl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N and halogen, C3 -C9 aryl-alkyl which is unsubstituted or substituted by substituents independently selected from the group consisting of OH, O, N and halogen;

    Z is --CHR7 --R11 --(CH2)m1 --C#(R8)((CH2)m2 (R9))--(CH2)m3 --R10 --(CH2)m4 --, --O--C6 H4 --CH2 --, --CHR7 --O--CHR7 --O--CHR7, --CHR7 --(CHR13)m1 --CHR14 --R10 --, ##STR24## R7 is H or C1 -C4 alkyl;

    R8 is H or C1 -C4 alkyl, C2 -C4 alkenyl, azidomethyl or azidoethyl;

    R9 is halogen (F, Cl, Br or I), H or OH;

    R10 is O, CH2 or a chemical bond;

    R11 is O, S, CH2, CHF, CF2 ;

    O is --C(R12)2 --CH2 --, --C(R12)--O--, --CR12

    CR12, or --C.tbd.C--, wherein each R12 is independently H, or halogen;

    R13 is H, halogen, OH, CH3, CH2 OH, or C3 -C12 acyloxymethyl;

    R14 is independently H, halogen, OH, CH3, CH2 OH, C3 -C12 acyloxymethyl, or C2-C12 acyloxy;

    R25 is CH2, CHF or O;

    R26 is CH or S, provided that when R25 is CH, R26 is not S;

    R27 is H, OH, halogen, N3, C1 -C4 alkoxy or when, R26 is S, R27 is absent;

    R27a is H, OH, halogen, N3, C1 -C4 alkyl, C1 -C4 alkoxy;

    R28 is H, OH, halogen, N3, C1 -C4 alkyl or C1 -C4 alkoxy;

    R29 is O, S, CH2, CHF, CF2 ;

    R32 is O;

    n2 is an integer having a value from 0 to 6;

    m1 is an integer having a value from 0 to 4;

    m2 is an integer having a value from 0 to 4;

    m3 is an integer having a value from 0 to 4;

    m4 is an integer having a value from 0 to 4;

    the carbon atom designated C# is in the R, S or RS configuration; and

    B is a base.

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